Skip to Content
Merck
CN

Key Documents

View All Documentation

158496

Proton-sponge®

99%

Synonym(s):

1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Linear Formula:
C10H6[N(CH3)2]2
CAS Number:
20734-58-1
Molecular Weight:
214.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849762
EC Number:
244-001-6
Beilstein/REAXYS Number:
396782
MDL number:
MFCD00003920
Assay:
99%
Form:
solid
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Segment

assay

99%

form

solid

mp

49-51 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)

functional group

amine

SMILES string

CN(C)c1cccc2cccc(N(C)C)c12

InChI

1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3

InChI key

GJFNRSDCSTVPCJ-UHFFFAOYSA-N

General description

Proton-sponge is a nucleophilic base used in alkoxycarbonylation, dehydrofluorination, arylation, and intramolecular cyclization reactions.

Proton-sponge is also referred to as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C2B8H14 and selected acyl chlorides. It has been tested as an effective H+ scavenger.

Application

Very strong base with weak nucleophilic character due to steric effects.
Proton-sponge can be used in the synthesis of C-substituted t-BuNH-8,9-R,R′-nido-7,8,9-C3B8H9 (R,R′ = H,H; MeH; Me,Me; Ph,H and Ph,Ph) tricarbollide compounds. It was also used in the preparation of saturated fluoroalkyl(hydrido) complexes of Iridium.

Legal Information

Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

235.4 °F - closed cup

Flash Point (°C)

113 °C - closed cup

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library